N, n&#39;, n&#39;&#39;-triacylmelamines



Patented May 16, 1950 N,N' ,N" -TRIACYLMELAMIN ES William S. Emerson andTracy M. Patrick, J15, Dayton, Ohio, assignors to Monsanto ChemicalCompany, St. Louis, Mo., a corporation of Delaware - N Drawing.

This invention relates to certain new triacylmelamines.

An object of this invention is to provide new triacylmelamines havingthe following structural formula:

The triacylmelamines of the above formula possess as a class aresistance to hydrolysis which is not shared by the lowertriacylmelamines, that is, those where R in the above formula has avalue of less than 4 carbon atoms. The present compounds also possess alower melting point than that possessed by the lower acyl members,

Application November 27, 1946,; 'Serial No. 712,738

- 4 Claims. (Cl. 260-2495) of the desired product; 'It has beenfound'desirable to employ efiicient stirring of the mixture during theheating period.

At the completion of the reaction, the reaction mixture is diluted withsome solvent such as methanol, ethanol, acetone or ethyl acetate, andthen filtered. This treatment serves to remove any unreacted anhydride.The residual solid is then washed with additional solvent and dried toobtain the crude product. Further purification may be efiected bycrystallization from glacial acetic acid or from any of the anhydridesused in the preparation of the compound in question.

For the production of the present triacylmelamines, any anhydridederived from an aliphatic mono-carboxylic acid above butyric in numberof, carbon atoms and including stearic and oleic acid anhydrides may beused. The acid anhydrides may be derived from saturated acids,unsaturated acids of either straightor branchedchain character.

In the manner described above, the following acid anhydrides werereacted with melamine: valeryl, isovaleryl, caproyl, oenanthyl, capryl,pelargonyl, lauryl, stearyl and oleyl to give the corresponding N,N',N''-triacylmelamine.

The reaction conditions, including temperature, time and yield, togetherwith the melting point of the particular triacylmelamine prepared, aregiven in the following table:

Table Reaction Reaction Oalcd. Found Melamine, Anhydnde, Yield, M. P.,Melamine Prepared moles m 0165 Tlgn ap, 1 3, Per Cent e 7 PerNGent Pergem;

N,N',N-Tri-n-valeryl 0. 008 0. 081 170-175 30 94 228-229 22. 2 22. 4N,N,N-Triisovalery1 0. 0016 0. 019 165-170 15 2162l8 22. 2 21. 8N,N,N-Tricaproyl 0. 008 0. 079 175 15 91 220 20. 0 l9, 9N,N',N-Irioenanthyl 0. 008 0. 083 5 90 210 18. 2 l8. 2 N,N,N-Tricaprylyl0. 008 0. 074 15 94 209 16. 7 16. 7 N,N,N-Tripelargony 0.008 0. 050 5 88194-95 15. 4 15. 3 N, N-Trilauryl 0. 004 0. 026 -195 15 99 178-179 12. 512. 5 N,N,N-Tristearyl 0. 150 0. 526 200 30 93 159-161 9. 08 9. 66N,N,N"-Tricleyl 0. 008 0. 032 195200 30 99 138-140 9. l4 9. 49

What we claim is: 1. Compounds having the formula:

4 where R is an alkyl group of from 4 to 17 carbon 4.N,N',N"-Trioleylmelamine, a compound atoms. having the structure oB. 0H,,oH=cH 0H,)1- o-NH=-o ClENH--(OHQQ 'H= H( Hm n N W aNH-J-(CH2)1CH=CH(CH|)1CH;

2. N,N,N"-Tristearylmela;mine; a compound 1o WILLIAM S. EMERSON. havingthe structure TRACY M. PATRICK, JR.

O CH 0 REFERENCES CITED CN C-NH- H l H l I I! t The following referencesare of record in the 0 file of this patent:

f E UNITED STATES PATENTS Number Name Date 3; N,N.,N"-Tri1aurylmelamine,a compound 2,165,265 Hubert May 21, 1936 having the structure in2,273,687 Bock Feb. 1'7, 1942 N 2,381,121 Ericks Aug. 7, 1945CH;(CH:)w-C -NHC c NH cH, wcH, OTHER REFERENCES 1 Ostrogovich, ChemicalAbstracts, vol. 30 (1936 25 pp. 465 and 466.

1% Textile Colorist, Jan. 1944, pp. 34 and 35. NEE-C-(CHzhoCHs

1. COMPOUNDS HAVING THE FORMULA: